Triethylamine → HCID 58610201, compound

HRID 1592835Notes

Reaction equation

HRID 1592835 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[F:7][C:8]1[CH:9]=[C:10]([C@H:14]([C@H:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17]2)[OH:15])[CH:11]=[CH:12][CH:13]=1.Cl.[F:30][C:31]1[CH:32]=[C:33]([C@@H:37]([C@@H:39]2[O:44][CH2:43][CH2:42][N:41]([CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:40]2)[OH:38])[CH:34]=[CH:35][CH:36]=1.C(N(CC)CC)C>ClCCl.O>[CH3:1][S:2]([O:15][C@H:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([F:7])[CH:9]=1)[C@H:16]1[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17]1)(=[O:4])=[O:3].[CH3:1][S:2]([O:38][C@@H:37]([C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([F:30])[CH:32]=1)[C@@H:39]1[O:44][CH2:43][CH2:42][N:41]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:40]1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69433256HCID 69433256, compoundHCID 69435002HCID 69435002, compound

Product 2

HCID 58610178HCID 58610178, compoundHCID 58610201HCID 58610201, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (1.01 g, 8.9 mmol) was added dropwise over 5 min to a stirred solution of (R)-[3-fluorophenyl][(2S)-4-benzylmorpholin-2-yl]methanol hydrochloride and (S)-[3-fluorophenyl][(2R)-4-benzylmorpholin-2-yl]methanol hydrochloride (1.50 g, 4.44 mmol) and triethylamine (1.79 g, 17.8 mmol) in dry dichloromethane (30 ml) at room temperature under nitrogen atmosphere. After 1 h, water (30 ml) was added, stirred vigorously and then the dichloromethane layer separated. The solution was dried over sodium sulphate, filtered and evaporated to a colourless oil. The oil was purified by chromatography on silica eluting with diethyl ether:hexane 3:1 to give (R)-[3-fluorophenyl][(2S)4-benzylmorpholin-2-yl]methyl methanesulphonate and (S)-[3-fluorophenyl][(2R)-4-benzylmorpholin-2-yl]methyl methanesulphonate as a colourless oil (1.51 g, 90%)

Workup

  1. customthe dichloromethane layer separated
  2. dry with materialThe solution was dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated to a colourless oil
  5. customThe oil was purified by chromatography on silica eluting with diethyl ether:hexane 3:1

Sources & evidence

ORD record
ord-2e547c40e27f437da94a265bb67000d5
Source dataset
uspto-grants-2007_11
Patent number
US07294623B2

Reaction notes

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