Triethylamine → (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl methanesulfonate

HRID 2363447Notes

Reaction equation

HRID 2363447 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([OH:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:16][C@@H:13]1[C@H:11]2[C@H:10]([CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12]2)[CH2:15][CH2:14]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57690431(3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol

Product 1

HCID 86659285(3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3aS,4S,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-ol (1.476 g, 6.79 mmol) from Step B and triethylamine (1.420 mL, 10.19 mmol) were combined in dichloromethane (30 mL). Methanesulfonyl chloride (0.635 mL, 8.15 mmol) was added as a solution in 20 mL of dichloromethane dropwise via addition funnel. The reaction was stirred at room temperature for 30 minutes and concentrated. The crude material was absorbed onto silica gel and chromatographed on a silica gel cartridge (Analogix®, Burlington, Wis., RS25-25) eluting with 20-100% ethyl acetate/hexanes to give (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl methanesulfonate: 1H NMR (300 MHz, CDCl3) δ ppm 7.35-7.27 (m, 4H), 7.27-7.20 (m, 1H), 4.96 (ddd, J=6.1, 7.6, 9.1, 1H), 3.71-3.44 (m, 1H), 2.94 (s, J=13.5, 3H), 2.85 (ddd, J=4.9, 8.1, 16.0, 1H), 2.75-2.68 (m, 2H), 2.67-2.55 (m, 1H), 2.54-2.44 (m, 1H), 2.31 (dd, J=4.1, 8.7, 1H), 2.20-2.04 (m, 1H), 1.97 (dtd, J=3.4, 6.2, 9.6, 1H), 1.79-1.63 (m, 1H), 1.61-1.49 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe crude material was absorbed onto silica gel
  3. customchromatographed on a silica gel cartridge (Analogix®, Burlington, Wis., RS25-25)
  4. washeluting with 20-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4de1a8a871a34db8baf2b855d198747d
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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