Water → HCID 68997756, compound

HRID 1909770Notes

Reaction equation

HRID 1909770 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].CCO[C:20]([CH3:22])=[O:21].O.[CH3:24][N:25]([CH:27]=O)C>>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][O:11][C:24]1[CH:6]=[CH:4][C:5]([C:20](=[O:21])[C:22]2[CH:14]=[CH:13][CH:12]=[CH:9][CH:10]=2)=[CH:27][N:25]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 68997756HCID 68997756, compoundYield 29%

Procedure

To a solution of N—BOC-L-prolinol (500 mg, 3.25 mmol) in anhydrous DMF (7 ml) was added NaH (124 mg, 60% dispersion in oil, 3.1 mmol) and stirred for 15 min at rt. A solution of product from Example 140, step 2 (364 mg, 1.68 mmol) in anhy.DMF (5 ml) was added dropwise over 5 min. The mixture was stirred at rt for 48 h. The mixture was poured into EtOAc and water, the organic layer dried over MgSO4, and concentrated. Silica gel flash chromatography using EtOAc/hexanes gave the title compound (185 mg, 29%).

Workup

  1. stirringThe mixture was stirred at rt for 48 h
  2. dry with materialthe organic layer dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bdf79d47b5c0485fb5f1fb760f4cfb36
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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