Dichloromethane → HCID 70664378, compound

HRID 1808732Notes

Reaction equation

HRID 1808732 reaction equation
ClCCl.[OH:4][C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]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:7]1[CH2:8][CH2:9][C@H:5]([OH:4])[CH2:6]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

Conditions

Temperature
0 °C

Procedure

To a dichloromethane (200 mL) and diethyl ether (200 mL) solution of (S)-3-hydroxypyrrolidine (19.8 mL, 244 mmol) and triethylamine (45.0 mL, 323 mmol) at 0° C. was added tert-butyl isocyanate (28.0 mL, 245 mmol). The reaction mixture was stirred for 1 hour at 0° C., filtered, and concentrated in vacuo to afford the title compound as a white solid. This crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 4.50-4.45 (m, 1H), 3.50-3.34 (m, 4H), 2.08-1.93 (m, 2H), 1.35 (s, 9H); LC-MS: m/z 187.3 (M+H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e66142ce36ac414fa366e09235bc546d
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

Loading…