Dichloromethane → HCID 86670528, compound

HRID 1808731Notes

Reaction equation

HRID 1808731 reaction equation
ClCCl.C(=O)(O)[O-].[Na+].[NH:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1.Cl[C:16]([O:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:17]>O>[OH:14][C@H:11]1[CH2:12][CH2:13][N:9]([C:16]([O:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:17])[CH2:10]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 33521852,2-Dimethylpropyl carbonochloridate

Product 1

HCID 86670528HCID 86670528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of dichloromethane (5 mL) and water (5 mL) was added sodium bicarbonate (0.96 g, 11 mmol), followed by (3S)-pyrrolidin-3-ol (1.00 g, 11.5 mmol). Neopentyl chloroformate (1.71 mL, 11.5 mmol) was then added dropwise, and the resulting suspension was stirred at room temperature for 1.5 hours. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 4.50 (br s, 1H), 3.81-3.77 (m, 2H), 3.59-3.41 (m, 4H), 2.07-1.96 (m, 2H), 1.75-1.72 (m, 1H), 0.97 (s, 9H).

Workup

  1. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7e4169f6dfa94c679a25563995872415
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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