Sodium borohydride → HCID 66673152, compound

HRID 747957Notes

Reaction equation

HRID 747957 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)[CH:7]=[CH:6][C:5]1=2>CO>[OH:3][CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)[CH:7]=[CH:6][C:5]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59750647HCID 59750647, compound2×

Product 1

HCID 66673152HCID 66673152, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add NaBH4 (79.4 mg, 2.10 mmol) to a suspension of 6-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (Intermediate 2, 395 mg, 1.40 mmol) in MeOH (10 ml), stirring at ambient temperature. After 24 hours, concentrate the reaction mixture and redissolve in EtOAc. Wash with 5% aqueous KOH, water, and brine before drying (MgSO4) and concentrating to a solid. Purify material on silica gel (50% THF/DCM) to give 6-(5-Hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (288 mg) as a white solid. Mass spectrum (ion spray): m/z=285 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.16 (d, 1H), 7.50 (d, 1H), 6.97 (m, 2H), 6.88 (s, 1H), 5.95 (broad, 2H), 4.80 (t, 1H0, 2.82-2.74 (m, 2H), 2.03-1.77 (m, 4H), 1.68 (s, 1H).

Workup

  1. concentrationconcentrate the reaction mixture
  2. dissolutionredissolve in EtOAc
  3. washWash with 5% aqueous KOH, water, and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating to a solid

Sources & evidence

ORD record
ord-841c8c90d26f4fc498b5dcde25457462
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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