Benzyl chloroformate → HCID 178523817, compound

HRID 1612883Notes

Reaction equation

Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>>[C:11]([NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 178479278HCID 178479278, compound

Product 1

HCID 178523817HCID 178523817, compoundYield 88%

Procedure

Commercially available trans-4-aminocyclohexanol hydrochloride (50 g, 0.33 mol) was treated with benzyl chloroformate (Cbz-Cl) (51.8 mL, 0.36 mol) under standard Schotten-Baumann conditions to provide N-Cbz-trans-4-aminocyclohexanol (62.33 g, 88% yield) as a white solid: m.p. 160°-162° C.; 1H NMR (300 MHz) δ 7.36 (m, 5H), 5.10 (s, 2H), 4.58 (br, 1H), 3.61 (m, 1H), 3.51 (m, 1H), 2.01 (br t, 4H, J=13.5 Hz), 1.40 (m, 2H), 1.20 (m, 2H); MS: (M+H)+ =250, (M+H+NH3)+ =267.

Sources & evidence

ORD record: ord-5c7a3b175b994b4d8d31d5a76841fc59
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190922

Reaction notes

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