Hydrochloric Acid → [6-(Hydroxymethyl)-3-cyclohexenyl]-N-octadecylformamide

HRID 566419Notes

Reaction equation

HRID 566419 reaction equation
[CH2:1]([N:19]1[C:27](=O)[CH:26]2C(C[CH:23]=[CH:24][CH2:25]2)[C:20]1=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[CH:31]([OH:33])[CH3:32].[BH4-].[Na+].Cl>O>[OH:33][CH2:31][CH:32]1[CH:27]([N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:20]=[O:29])[CH2:26][CH:25]=[CH:24][CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 212661442-Octadecyl-4,7,3a,7a-tetrahydroisoindole-1,3-dione

Product 1

HCID 86756229[6-(Hydroxymethyl)-3-cyclohexenyl]-N-octadecylformamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Octadecyl-4,7,3a,7a-tetrahydroisoindole-1,3-dione (5.00 g) was suspended into a mixture of 2-propanol (90 ml) and water (15 ml) and then sodium borohydride (2.34 g) was added thereto. After being stirred for 46 hours at room temperature, the reaction mixture was acidified with dilute hydrochloric acid and then concentrated. The residue was, with chloroform added thereto, washed with dilute hydrochloric acid, water and saturated sodium hydrogencarbonate aqueous solution successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (silica gel 80 g, chloroform:methanol=50:1-10:1), thereby yielding the entitled compound (4.32 g) as white crystals.

Workup

  1. concentrationconcentrated
  2. additionadded
  3. washwashed with dilute hydrochloric acid, water and saturated sodium hydrogencarbonate aqueous solution successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (silica gel 80 g, chloroform:methanol=50:1-10:1)

Sources & evidence

ORD record
ord-a05458d6b26d497282ef231344e0aa16
Source dataset
uspto-grants-2001_01
Patent number
US06174885B1

Reaction notes

Loading…