Sodium hydride → (R)-benzyl 1-hydroxy-3-(2-oxopyrrolidin-1-yl)propan-2-ylcarbamate

HRID 451820Notes

Reaction equation

HRID 451820 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH2:8][C@@H:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][OH:11])=[O:6].[H-].[Na+]>CN(C=O)C>[OH:11][CH2:10][C@H:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][N:7]1[CH2:2][CH2:3][CH2:4][C:5]1=[O:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86639450(R)-benzyl 1-(4-chlorobutanamido)-3-hydroxypropan-2-ylcarbamate

Product 1

HCID 59201635(R)-benzyl 1-hydroxy-3-(2-oxopyrrolidin-1-yl)propan-2-ylcarbamateYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-benzyl 1-(4-chlorobutanamido)-3-hydroxypropan-2-ylcarbamate (3.9 g, 11.9 mmol) in DMF was cooled to 0° C., followed by the addition of NaH (0.72 g, 17.9 mmol). The mixture was stirred at rt for 4 h. DMF was removed under high vacuum, and the residue was taken up in EtOAc, washed with 1 N HCl, saturated NaHCO3, NaCl, dried over Na2SO4, and concentrated to give the crude product, which was purified by column chromatography to give (R)-benzyl 1-hydroxy-3-(2-oxopyrrolidin-1-yl)propan-2-ylcarbamate (1.1 g, yield 33%). 1H NMR (CDCl3, 400 MHz) δ 7.39-7.27 (m, 5H), 5.45 (d, 1H), 5.10 (d, 1H), 4.70 (s, 2H), 3.72 (m, 1H), 3.54-3.40 (m, 4H), 3.20-3.17 (m, 1H), 2.40 (t, 2H), 2.07 (t, 2H).

Workup

  1. customDMF was removed under high vacuum
  2. washwashed with 1 N HCl, saturated NaHCO3, NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8961601b2182411292807a2e54076422
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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