Benzyl chloroformate → HCID 90910790, compound

HRID 1948306Notes

Reaction equation

HRID 1948306 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[NH2:13][C@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][C@H:15]1[O:25][CH3:26]>C([O-])(O)=O.[Na+]>[CH2:5]([O:4][C:2]([NH:13][C@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][C@H:15]1[O:25][CH3:26])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 131730313HCID 131730313, compound2×

Product 1

HCID 90910790HCID 90910790, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Benzyl chloroformate (3.3 ml) was added dropwise to a cold solution of Cis(±)ethyl 4-amino-3-methoxypiperidine-1-carboxylate hydrochloride salt (Intermediate 21; 5 g) in saturated NaHCO3. The mixture was stirred at room temperature for 14 h. The white precipitate was filtered, washed well with water, dried in vacuo to give the title compound as a white solid (6.66 g). MS (ES) MH+: 336 for C17H24N2O5; NMR: 1.21 (t, 3H), 1.52-1.67 (m, 2H), 3.08 (m, 2H), 3.28 (s, 3H), 3.41 (s, 2H), 3.74-3.92 (m, 2H), 3.96 (m, 2H), 4.14 (m, 1H), 5.10 (s, 2H), 7.24 (d, 1H), 7.44 (m, 5H).

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed well with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a1dbebcb040d4b66865435f08cd6156b
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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