Benzylamine → ethyl 2-(2-benzyloctahydro-1H-isoindol-1-yl)acetate

HRID 60835Notes

Reaction equation

HRID 60835 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH2:16]([N:23]1[CH2:1][CH:3]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH:9]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 89748227(E)-ethyl 3-(2-formylcyclohexyl)acrylate

Product 1

HCID 21858214ethyl 2-(2-benzyloctahydro-1H-isoindol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-ethyl 3-(2-formylcyclohexyl)acrylate, benzyl amine and NaBH(Oac)3 in DCM was stirred at rt for 3 h. The reaction mixture was quenched with saturated NaHCO3. The organic layer was separated and the aqueous layer was extracted with DCM (2×). All organic layers were combined, dried with dried with MgSO4 and concentrated in vacuo to give the crude product which was purified by chromatography to afford desired ethyl 2-(2-benzyloctahydro-1H-isoindol-1-yl)acetate. MS (ESI) 302 (M+H).

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×)
  4. customdried
  5. dry with materialwith dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-b7c2b5d64b6d46d09f87cac84db17eab
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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