Dichloromethane → HCID 70664378, compound

HRID 514880Notes

Reaction equation

HRID 514880 reaction equation
ClCCl.[NH:4]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5]1.C(N(CC)CC)C.[C:17]([N:21]=[C:22]=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(OCC)C>[C:17]([NH:21][C:22]([N:4]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 70664378HCID 70664378, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dichloromethane (100 mL)/diethyl ether (200 mL) solution of (S)-pyrrolidin-3-ol (9.80 mL, 121 mmol) and triethylamine (21.9 mL, 157 mmol) at 0° C. was added tert-butyl isocyanate (13.8 mL, 121 mmol). The reaction mixture was stirred for 30 minutes and concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 4.54-4.38 (m, 1H), 4.10 (br s, 1H), 3.48-3.32 (m, 5H), 2.06-1.95 (m, 2H), 1.35 (s, 9H); LC-MS: m/z 187.3 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-158c0f4cb60546d982e8625e4a6e5204
Source dataset
uspto-grants-2015_08
Patent number
US09108920B2

Reaction notes

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