Tert-Butylamine → HCID 54010308, compound

HRID 1734664Notes

Reaction equation

HRID 1734664 reaction equation
Br[C:2]1[N:6]([CH:7]2[CH:11]([OH:12])[CH:10]([OH:13])[CH:9]([CH2:14][OH:15])[CH2:8]2)[C:5]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:4]=2[N:3]=1.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23]>>[C:22]([NH:26][C:2]1[N:6]([CH:7]2[CH:11]([OH:12])[CH:10]([OH:13])[CH:9]([CH2:14][OH:15])[CH2:8]2)[C:5]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:4]=2[N:3]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 20083552HCID 20083552, compound

Product 1

HCID 54010308HCID 54010308, compound

Conditions

Temperature
90 °C

Procedure

A solution of (±)-(1R*, 2S*, 3S*, 5S*)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-3-(hydroxymethyl)-1,2-cyclopentanediol (750 mg, 1.44 mmole) was stirred in tert-butylamine (Aldrich, 98%, 25 mL) in a Parr bomb maintained at 90° C. (oil bath) for 6 days. Volatiles were evaporated in vacuo and the residual solids refluxed in ethanol (30 mL) with aqueous dimethylamine (Aldrich, 40%, 2 mL) for one hour. Volatiles were evaporated and the residual solids chromatographed on silica gel. Elution with 10% methanol-ethyl acetate gave title compound as colorless glass. Solidification from water gave (±)-(1R*, 2S*, 3S*, 5S*)-5-[2-(tert-butylamino )-5,6-dichloro-1H-benzimidazol-1-yl]-3-(hydroxymethyl)-1,2-cyclopentanediol as a white powder (150 mg, 26%); m.p. 130°-132° C.; 1H-NMR(DMSO-d6) identical with that of the enatiomer described in Example 82.

Workup

  1. customVolatiles were evaporated in vacuo
  2. temperaturethe residual solids refluxed in ethanol (30 mL) with aqueous dimethylamine (Aldrich, 40%, 2 mL) for one hour
  3. customVolatiles were evaporated
  4. customthe residual solids chromatographed on silica gel
  5. washElution with 10% methanol-ethyl acetate

Sources & evidence

ORD record
ord-6709cd4242cb4a52913528d84f52480a
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

Loading…