Sodium triacetoxyborohydride → HCID 42602987, compound

HRID 1942419Notes

Reaction equation

HRID 1942419 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1)[CH2:2][CH3:3].[C:14]12([NH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH:29]=O)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:14]12([NH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][N:4]([CH2:1][CH2:2][CH3:3])[CH:5]3[CH2:13][CH2:12][C:8]4[N:9]=[CH:10][S:11][C:7]=4[CH2:6]3)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 16100282HCID 16100282, compoundHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

Product 1

HCID 42602987HCID 42602987, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 395 mg (2 mmol) propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine and 748 mg (3 mmol) N-adamantyl-5-oxopentanamide in 1,2-dichloroethane (20 mL) is stirred for about 30 minutes. Then 0.75 g (3 mmol) of sodium triacetoxyborohydride is added and the mixture is stirred overnight. After hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated, dried over sodium sulfate and concentrated in vacuum. The crude product obtained is purified via column chromatography on silica gel.

Workup

  1. customAfter hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-3ba822e502e146b9b3fc7e3ca0f6ee33
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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