HCID 118222041, compound → HCID 118222055, compound

HRID 713144Notes

Reaction equation

HRID 713144 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]([OH:20])[CH2:17][CH:18]=[CH2:19])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C=C>C(Cl)Cl>[OH:20][CH:16]1[CH2:17][CH:18]=[CH:19][CH2:1][N:4]([C:5]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:14])[CH2:15]1

Participants

3

Reactant 1

HCID 118222041HCID 118222041, compound

Product 1

HCID 118222055HCID 118222055, compoundYield 47.47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of benzyl N-allyl-N-(2-hydroxypent-4-enyl)carbamate (6.10 g, 22.15 mmol, 1.00 Eq) in DCM (400 mL) was added Zhan catalyst 1B (812.63 mg, 1.11 mmol, 0.05 Eq) under N2 protection. The mixture was stirred at 25° C. for 16 hr under N2 protection. Then TLC detected the reaction was completed, the solvent was evaporated, the residue was purified by chromatography (silica gel, eluting with PE:EA=2:1) to afford benzyl 3-hydroxy-2,3,4,7-tetrahydroazepine-1-carboxylate (2.60 g, 10.51 mmol, 47.47% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.30-7.46 (m, 5H), 5.63-5.89 (m, 2H), 5.19 (s, 2H), 3.96-4.13 (m, 2H), 3.74-3.90 (m, 2H), 3.54-3.70 (m, 1H), 2.43 (m, 2H).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by chromatography (silica gel, eluting with PE:EA=2:1)

Sources & evidence

ORD record
ord-9a4b714b18da45abb7ca156f025def2d
Source dataset
uspto-grants-2015_11
Patent number
US09181288B2

Reaction notes

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