Diboron → N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

HRID 1587945Notes

Reaction equation

HRID 1587945 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[C:21](=O)[CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:31])([F:30])[F:29])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].B#B>O1CCCC1>[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[CH2:21][CH2:20][O:19][CH:18]([C:23]3[N:24]=[C:25]([C:28]([F:29])([F:31])[F:30])[S:26][CH:27]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6328200DiboronHCID 19974202N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one

Product 1

HCID 19974360N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 g (0.0022 Mol) of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholin-5-one (diastereomer A) is dissolved in 6 ml of absolute tetrahydrofuran. At room temperature 15 ml (0.015 Mol) of a one molar solution of diborane in tetrahydrofuran is added dropwise within 15-20 minutes. During this the solution heated up to about 35°-40° C. After 30 minutes the mixture is evaporated to dryness and the remaining residue is dissolved in 40 ml of methanol and 2 ml of concentrated hydrochloric acid, and the mixture is left to stand for 30 minutes. While cooling in ice, the mixture is made alkaline with ammonia and is extracted several times by shaking with methylene chloride. The organic phase is dried over sodium sulphate and the base is purified on a silica gel column using toluene/ethyl acetate=7.5:2.5 as eluant.

Workup

  1. temperatureDuring this the solution heated up to about 35°-40° C
  2. customAfter 30 minutes the mixture is evaporated to dryness
  3. dissolutionthe remaining residue is dissolved in 40 ml of methanol
  4. wait2 ml of concentrated hydrochloric acid, and the mixture is left
  5. temperatureWhile cooling in ice
  6. extractionis extracted several times
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe base is purified on a silica gel column

Sources & evidence

ORD record
ord-faa83ed9604e4371800d86ace70d5351
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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