Hexane → Boc-L-Pro-Ome

HRID 350377Notes

Reaction equation

HRID 350377 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16]CCCCC.[Si](C=[N+]=[N-])(C)(C)C>CO.C1C=CC=CC=1>[CH3:16][O:11][C:10](=[O:12])[C@@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 3

HCID 8058HexaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 167693Trimethylsilyldiazomethane

Product 1

HCID 1277666Boc-L-Pro-OmeYield 100%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a stirred solution of the N-tert-butoxycarbonylproline (6.00 g, 0.0279mol) in MeOH:benzene (1:4, v/v) was added dropwise 2.0 M-n-hexane solution of TMSCHN2 (16.7 mL, 0.0334mol) at room temp. After the resulting solution was stirred for 1 hr at room temp, the mixture was evaporated off in vacuo to afford 6.39 g (100%) N-tert-butoxycarbonylproline methyl ester as a yellow syrup. 1H-NMR (CDCl3) δ 1.41 (s, 9H), 1.85–1.98 (m, 4H), 2.21–2.28 (m, 2H), 3.72 (s, 3H), 4.29 (m, 1H).

Workup

  1. customthe mixture was evaporated off in vacuo

Sources & evidence

ORD record
ord-b68805075c07415b808f4d908ef0ba6f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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