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Acetic Acid → Ethyl 1-((4-methoxy-2,3,5-trimethylphenylamino)methyl)-cyclobutanecarboxylate

HRID 2103063
Notes
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Reaction equation

HRID 2103063 reaction equation
[CH3:1][O:2][C:3]1[C:9]([CH3:10])=[CH:8][C:6]([NH2:7])=[C:5]([CH3:11])[C:4]=1[CH3:12].[CH:13]([C:15]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCl.O>[CH3:1][O:2][C:3]1[C:9]([CH3:10])=[CH:8][C:6]([NH:7][CH2:13][C:15]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]2)=[C:5]([CH3:11])[C:4]=1[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12226109Ethyl 1-formylcyclobutanecarboxylateHCID 147002344-Methoxy-2,3,5-trimethylaniline

Product 1

HCID 86605498Ethyl 1-((4-methoxy-2,3,5-trimethylphenylamino)methyl)-cyclobutanecarboxylate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2,3,5-trimethylaniline (400 mg) in dichloromethane (24 mL) was added ethyl 1-formylcyclobutanecarboxylate, prepared as described in Step 1 (377.8 μL). Then NaBH(OAc)3 (771.4 mg) and acetic acid (152.2 μL) were added sequentially. After 3.5 h, water was added. The two layers were separated and the aqueous layer was extracted with more dichloromethane. The combined organic phases were washed with brine, dried and evaporated. Elution of the residue on a silica column (EtOAc/DCM, 0-5%) gave ethyl 1-((4-methoxy-2,3,5-trimethylphenylamino)methyl)-cyclobutanecarboxylate (400 mg) as an oil. 1H-NMR, (300 MHz, CDCl3) δ=6.37 (s,1H), 4.262-3.974 (q, 2H), 3.63 (s, 3H), 3.745-3.474 (br s, 1H), 3.41 (s, 2H), 2.693-2.339 (m, 2H), 2.27 (s, 3H), 2.21, (s, 3H), 2.14-1.818, (m, 4H), 2.02, (s, 3H), 1.333-1.174 (t, 3H) ppm., 13C-NMR, (75 MHz, CDCl3) δ=176.51, 142.52, 129.68, 128.09, 119.78, 110.29, 60.85, 60.37, 50.67, 47.2, 28.43, 16.38, 15.9, 14.3, 12.94, 12.85 ppm.

Workup

  1. customprepared
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with more dichloromethane
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. customevaporated
  7. washElution of the residue on a silica column (EtOAc/DCM, 0-5%)

Sources & evidence

ORD record
ord-ca1eeb87eb074c43a2518b04b25edb76
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576094B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes