Water → HCID 15016533, compound

HRID 1460742Notes

Reaction equation

HRID 1460742 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:13][CH2:12][C@@H:11]([CH2:14]O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>C(Cl)Cl>[C:1]1([C@H:7]([N:9]2[CH2:13][CH2:12][C@@H:11]([CH2:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13772858{(3R)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

Product 1

HCID 15016533HCID 15016533, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (3R)-1-[(R)-1-phenylethyl]-3-(hydroxymethyl)pyrrolidine (25.2 g, 0.12 mol) in CH2Cl2 (250 mL) was added Et3N (18.8 mL, 0.13 mol). The mixture was cooled to 0° C. and treated dropwise with methanesulfonyl chloride (10.63 mL, 0.13 mol) dissolved in CH2Cl2 (125 mL). The mixture was stirred at 0° for 1.5 hours and then at 25° C. for 4 hours. Water was added and the organic layer was separated, washed with NaHCO3 (2X), dried (MgSO4) and concentrated to provide (3R)-1-[(R)-1-phenylethyl]-3-(methanesulfonyl methyl)-pyrrolidine (2a. 33.2 g); NMR (CDCl3) δ 1.39 (m, 3H), 1.54 (m, 1H), 2.0 (m, 1H), 2.3-2.8 (m, 5H), 2.98 (d, 3H), 3.29 (q, 1H), 4.14 (t, 2H), 7.31 (m, 5H). The material was used directly in the next step.

Workup

  1. waitat 25° C. for 4 hours
  2. customthe organic layer was separated
  3. washwashed with NaHCO3 (2X)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-164c93938ac94fccbe5b4e90609c6287
Source dataset
uspto-grants-1991_12
Patent number
US05072001

Reaction notes

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