Formic Acid → HCID 10707397, compound

HRID 1034518Notes

Reaction equation

HRID 1034518 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18](O)=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][CH:18]=[O:19])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 10707397HCID 10707397, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine (7.36 g: 30 mmole) in tetrahydrofuran (30 ml), formic acid (1.36 ml: 36 mmole), triphenylphosphine (9.44 g: 36 mmole) and diethyl azodicarboxylate (5.67 ml: 36 mmole) are successively added in a nitrogen atmosphere under ice cooling. The mixture is stirred to react for 40 minutes at the same temperature to give (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine (5.38 g). Yield: 66%. Colorless crystals. NMR δ(CDCl3) ppm: 1.45(d, J=8.6 Hz, 9H), 2.2 to 2.4(m, 1H), 2.4 to 2.7(m, 1H), 3.5 to 3.9(m, 2H), 3.75(s, 3H), 4.3 to 4.6(m, 1H), 5.3 to 5.5(m, 1H), 7.98 (s, 1H). IR ν (KBr) cm-1 : 3420, 1748, 1712, 1681.

Workup

  1. customto react for 40 minutes at the same temperature

Sources & evidence

ORD record
ord-f3a46bd0b5f940ab88826030e9a383ad
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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