Methanol → HCID 22882355, compound

HRID 863295Notes

Reaction equation

HRID 863295 reaction equation
[BH4-].[Li+].[CH2:3]([O:10][CH2:11][C:12]1([CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17](OC)=[O:18])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO>O1CCCC1>[CH2:3]([O:10][CH2:11][C:12]1([CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][OH:18])[CH2:13][CH2:14]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 22882354HCID 22882354, compound

Product 1

HCID 22882355HCID 22882355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.3 g of lithium borohydride are added in portions to a solution of 30.9 g of 1-benzyloxymethyl-1-[2(S)-tert-butoxycarbonylamino-2-methoxycarbonyleth-1-yl]cyclopropane in 300 ml of tetrahydrofuran, while stirring. The mixture is stirred at room temperature for a further 2 h, 500 ml of methanol are then slowly added dropwise, the mixture is concentrated almost to dryness and the residue is taken up in methylene chloride. The organic phase is washed with 1N hydrochloric acid. Further customary working up gives the pure title compound: Rf (B)=0.50.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 2 h
  2. concentrationthe mixture is concentrated almost to dryness
  3. washThe organic phase is washed with 1N hydrochloric acid

Sources & evidence

ORD record
ord-5e94496b585147278efba07ba2370cd5
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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