Sodium triacetoxyborohydride → Ethyl 4-[cyclopropyl(oxetan-3-yl)amino]cyclohexane-1-carboxylate

HRID 574917Notes

Reaction equation

HRID 574917 reaction equation
[CH:1]1([NH:4][CH:5]2[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[O:16]1[CH2:19][C:18](=O)[CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([N:4]([CH:18]2[CH2:19][O:16][CH2:17]2)[CH:5]2[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

Product 1

HCID 67126835Ethyl 4-[cyclopropyl(oxetan-3-yl)amino]cyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 329A (1.05 g) in dichloromethane (10 mL) was added oxetan-3-one (0.358 g) followed by sodium triacetoxyborohydride (1.05 g). The mixture was stirred overnight. The mixture was diluted with dichloromethane (300 mL) and washed with 2N aqueous NaOH, water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with 2N aqueous NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-14a591eb0d24450187126a6561bcc58b
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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