ChemicalBook CAS DataBase List 83435-58-9

83435-58-9

Name	Boc-D-prolinol
CAS	83435-58-9
EINECS(EC#)	626-169-6
Molecular Formula	C10H19NO3
MDL Number	MFCD00040580
Molecular Weight	201.26
MOL File	83435-58-9.mol

Synonyms

BOC-D-PROLINOL BOC-D-PRO-OL BOC-(R)-2-(HYDROXYMETHYL) PYRROLIDINE N-ALPHA-T-BOC-D-PROLINOL N-BOC-D-PROLINOL N-T-BOC-D-PROLINOL N-T-BUTOXYCARBONYL-D-PROLINOL N-TERT-BUTOXYCARBONYL-D-PROLINOL (R)-(+)-1-BOC-2-PYRROLIDINEMETHANOL (R)-1-BOC-2-PYRROLIDINEMETHANOL (R)-(+)-1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINEMETHANOL (R)-2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (R)-(-)-N-BOC-PROLINOL (R)-N-TERT-BUTOXYCARBONYL PROLINOL 1-BOC-D-PROLINOL 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2R)- N-tert-Butoxycarbonyl-D-prolino N-BENZYL-D-PROLINOL N-alpha-t-Butyloxycarbonyl-D-prolinol, (R)-N-t-Butyloxycarbonyl-2-pyrrolidinemethanol BOC-D-PROLINOL LIQUID

Chemical Properties

Appearance	White powder
Melting point	60-64 °C (lit.)
alpha	49 º (589nm, =1.3, CHCl3)
Boiling point	289.5±13.0 °C(Predicted)
density	1.084±0.06 g/cm3(Predicted)
refractive index	54 ° (C=5, MeOH)
storage temp.	Store at 0°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Crystalline Powder
pka	14.77±0.10(Predicted)
color	White to light beige
Optical Rotation	[α]23/D +50°, c = 1.3 in chloroform
Water Solubility	insoluble
Major Application	peptide synthesis
InChI	InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h8,12H,4-7H2,1-3H3/t8-/m1/s1
InChIKey	BFFLLBPMZCIGRM-MRVPVSSYSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCC[C@@H]1CO
CAS DataBase Reference	83435-58-9(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319
Precautionary statements	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes	Xi,Xn
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
WGK Germany	3
HS Code	29051990
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

White powder

Uses

N-(tert-Butoxycarbonyl)-D-prolinol is used to prepare (azetidinyl)methoxy]pyridines and 2-(aryloxymethyl) azacyclic analogs with therapeutic potetials for the treatment of central nervous system (CNS) disorders.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

68832-13-3

24424-99-5

59378-81-3

Step 1: Dissolve (R)-2-(hydroxymethyl)pyrrolidine (2.0 g, 19.8 mmol) in dichloromethane (20 mL) and add 1 M aqueous sodium hydroxide solution (20 mL). A solution of di-tert-butyl dicarbonate (4.32 g, 19.8 mmol) in dichloromethane (10 mL) was added slowly and dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. After completion of the reaction, the organic and aqueous layers were separated. The organic layer was washed twice with distilled water and the aqueous layer was extracted with dichloromethane. All organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. Purification by recrystallization from hexane afforded the intermediate (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate in a yield of 2.60 g (65% yield).

References

[1] Patent: US5902819, 1999, A
[2] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 60
[3] European Journal of Organic Chemistry, 2002, # 14, p. 2391 - 2399
[4] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[5] Tetrahedron Asymmetry, 1997, vol. 8, # 13, p. 2209 - 2213

Spectrum Detail

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