Sodium borohydride → HCID 13223064, compound

HRID 1413822Notes

Reaction equation

HRID 1413822 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH3:20])([CH3:19])[C@@H:10]([OH:18])[C@H:11]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:21][CH:22]=1)[O:8][C:9]([CH3:20])([CH3:19])[C@@H:10]([OH:18])[C@@H:11]2[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13223045HCID 13223045, compound

Product 1

HCID 13223064HCID 13223064, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

6-Acetyl-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2H-benzo[b]pyran-3-ol (1.00 g) was dissolved in methanol (10 ml) and water (2 ml) and treated with sodium borohydride (0.10 g) with stirring at room temperature during 5 minutes. After an additional 2 hours stirring, the reaction mixture was diluted with water (100 ml). Extraction using diethyl ether gave 1-hydroxy-1-[trans-2,2-dimethyl-3-hydroxy-4-piperidinochroman-6-yl]-ethane (1.00 g) which was dissolved in dry ether and treated with ethereal hydrogen chloride giving the hydrochloride salt (0.90 g) m.p. 179°-181° C. as a white powder from ethanol-ether.

Workup

  1. stirringAfter an additional 2 hours stirring
  2. extractionExtraction

Sources & evidence

ORD record
ord-f1c344117f3245319f0a5782addac111
Source dataset
uspto-grants-1981_02
Patent number
US04251537

Reaction notes

Loading…