Sodium borohydride → HCID 54529640, compound

HRID 482773Notes

Reaction equation

HRID 482773 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14]([OH:16])[CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53803015HCID 53803015, compound

Product 1

HCID 54529640HCID 54529640, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2,5-dione (2.7 g) and sodium borohydride (0.2 g) in ethanol (100 ml) is stirred at room temperature for 18 hours. The solvent is removed under reduced pressure, and the residue dissolved in dichloromethane (100 ml). The solution is extracted with ice-cold 2N HCl (2×50 ml) and saturated brine (50 ml) and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue triturated with ether to give 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-5-hydroxy-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (100 ml)
  3. extractionThe solution is extracted with ice-cold 2N HCl (2×50 ml) and saturated brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue triturated with ether

Sources & evidence

ORD record
ord-8d70e89a6e0146dab2069fa82a8a17f2
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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