Sodium borohydride → HCID 20269010, compound

HRID 2417850Notes

Reaction equation

HRID 2417850 reaction equation
[NH:1]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:13])[CH2:5][CH2:4][CH2:3][C:2]1=[O:14].[BH4-].[Na+]>C(O)C>[OH:13][CH:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:1][C:2](=[O:14])[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122264031-Benzazocine-2,6(1H,3H)-dione, 4,5-dihydro-

Product 1

HCID 20269010HCID 20269010, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,5-dihydro-1-benzazocin-2,6-(1H,3H)dione (14.2 g), Tetrahedron Letters 4079-4082 (1976), and sodium borohydride (1.4 g) in ethanol (720 ml) is stirred at room temperature for 18 hours. The ethanol is removed under reduced pressure, and the residue dissolved in dichloromethane (350 ml). The solution is extracted with 2N hydrochloric acid (2×200 ml) and saturated brine (100 ml), and dried over sodium sulfate. The solvent is removed under reduced pressure to give 6-hydroxy-3,4,5,6-tetrahydro-1-benzazocin-2-(1H)-one.

Workup

  1. customThe ethanol is removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (350 ml)
  3. extractionThe solution is extracted with 2N hydrochloric acid (2×200 ml) and saturated brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-aa6ce958b5ec47e397d293c04fa82adf
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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