Dimethylamine → rac-(1R,2R)-2-(dimethylamino)cyclohexan-1-ol

HRID 1387032Notes

Reaction equation

HRID 1387032 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH3:8][NH:9][CH3:10].C1COCC1>CO>[CH3:8][N:9]([CH3:10])[C@@H:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[OH:7]

Participants

5

Conditions

Temperature
0 °C

Procedure

To a solution of cyclohexene oxide (3.64 mL, 36.0 mmol) in 30 mL of dry methanol was added dropwise 2.0 M dimethylamine in THF (15.0 mL, 30.0 mmol). The reaction mixture was stirred at 0° C. for 4 h. The solution was then warmed to room temperature and stirred for 18 h. The reaction mixture was then concentrated under reduced pressure to afford 1.11 g (26% crude yield) of the crude product which was used in the following reaction without purification.

Workup

  1. temperatureThe solution was then warmed to room temperature
  2. stirringstirred for 18 h
  3. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b5d47270940b4bc6b4aa2679cdc0ae0a
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…