N-BOC-ALPHA-METHYL-L-PROLINE Chemical Properties

Boiling point:

337.8±35.0 °C(Predicted)

Density 

1.160

storage temp. 

2-8°C

pka

4.20±0.20(Predicted)

form 

Solid

color 

White to off-white

InChI

InChI=1S/C11H19NO4/c1-10(2,3)16-9(15)12-7-5-6-11(12,4)8(13)14/h5-7H2,1-4H3,(H,13,14)/t11-/m0/s1

InChIKey

YQXRKJHVAUKXRN-NSHDSACASA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@@]1(C)C(O)=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

N-BOC-ALPHA-METHYL-L-PROLINE Usage And Synthesis

Uses

N-Boc-2-methyl-L-proline is used as pharmaceutical intermediate.

Synthesis

(S)-2-methylpyrrolidine-2-carboxylic acid hydrochloride (23; 82.5 g, 498 mmol) was dissolved in a solvent mixture of acetonitrile/water (1:1, 1000 mL) and triethylamine (TEA, 210 mL, 1490 mmol) was added. Subsequently, di-tert-butyl dicarbonate (Boc2O, 120 g, 548 mmol) dissolved in acetonitrile (200 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The organic solvent was removed by evaporation under reduced pressure and 2M aqueous sodium hydroxide (300 mL) was added to the residue. The aqueous phase was extracted with ether (Et2O, 400 mL), cooled to 10 °C and the pH was adjusted to 5-6 by slow addition of 25% aqueous hydrochloric acid. 1M aqueous hydrochloric acid was then carefully added to pH=2 and the product precipitated. The precipitate was collected by filtration, washed with water (300 mL), and dried under high vacuum to give (S)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (24, 90.7 g) as a light gray solid. lc-MS: tR = 0.63 min; [M + H]+ = 230.24.

References

[1] Tetrahedron Letters, 1996, vol. 37, # 20, p. 3441 - 3444
[2] Patent: WO2008/8551, 2008, A2. Location in patent: Page/Page column 34
[3] Patent: US2010/197654, 2010, A1. Location in patent: Page/Page column 57
[4] Organic Letters, 2011, vol. 13, # 22, p. 5964 - 5967
[5] Patent: WO2013/182972, 2013, A1. Location in patent: Page/Page column 110

N-BOC-ALPHA-METHYL-L-PROLINE(103336-06-7)Related Product Information

• N-Boc-trans-4-tosyloxy-L-proline methyl ester
• N-Boc-4-oxo-L-Proline methyl ester
• BOC-4,4-DIFLUORO-L-PROLINE METHYL ESTER
• (2S,4S)-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate hydrochloride
• (S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER
• N-Boc-cis-4-Hydroxy-L-proline methyl ester
• N-Boc-trans-4-Hydroxy-L-proline methyl ester
• N-BOC-CIS-4-CYANO-L-PROLINE METHYL ESTER
• BOC-HYP-OBZL
• BOC-(S)-ALPHA-(4-BIPHENYLMETHYL)-PROLINE
• BOC-(S)-ALPHA-(1-NAPHTHALENYLMETHYL)-PROLINE
• BOC-(R)-ALPHA-(3-PHENYL-PROPYL)-PROLINE
• BOC-L-TRANSPRO(4-CN)-OBN
• BOC-PRO-ONP
• BOC-(S)-ALPHA-BENZYL-PROLINE
• BOC-HYP-OTBU
• N-BOC-ALPHA-METHYL-L-PROLINE
• BOC-(R)-ALPHA-PHENETHYL-L-PROLINE