Tert-butyl 3-oxopyrrolidine-1-carboxylate → HCID 131727245, compound

HRID 1454338Notes

Reaction equation

HRID 1454338 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:14]([O-:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 3780918Diethylphosphite

Product 1

HCID 131727245HCID 131727245, compoundYield 53.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.9 g (10.3 mmol) of 1-tert-butoxycarbonyl-3-oxopyrrolidine (from Step B), 1.3 mL (10.3 mmol) of diethyl phosphite and 1.4 mL (10.3 mmol) of TEA was stirred at 100° C. for 1.5 h. Volatiles were removed under reduced pressure. The residue was purified on a 40M Biotage column using 13:7 v/v hexane/acetone as the eluant to afford 1.78 g (53%) of the title compound as a yellow oil: RF: 0.16 (7:3 v/v hexane/acetone); 1H-NMR (500 MHz) δ 1.33 (t, J=7.0, 6H), 1.45 (s, 9H), 2.08 (m, 1H), 2.18 (m, 1H), 3.47-3.64 (m, 4H), 4.13-4.22 (m, 4H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customThe residue was purified on a 40M Biotage column

Sources & evidence

ORD record
ord-8c2c0b4f7dd34eb29e588818b83292fa
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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