Acetic Acid → HCID 178445782, compound

HRID 713918Notes

Reaction equation

HRID 713918 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH:22]=O)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][CH2:25][C:26]#[N:27].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:27][CH2:26][C:25]#[N:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10901AminoacetonitrileHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178445787HCID 178445787, compound

Product 1

HCID 178445782HCID 178445782, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-((trans)-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (310 mg, 1 mmol), 2-aminoacetonitrile (112 mg, 2 mmol, 2.0 eq) and acetic acid (180 mg, 3 mmol, 3.0 eq) in DCE (10 mL) was stirred at rt for 10 min. Then NaBH(OAc)3 (636 mg, 3 mmol, 3.0 eq) was added to the mixture and the mixture was stirred at rt for 15 h. Then saturated NaHCO3 was added to the mixture until pH=8. The mixture was extracted with DCM (20 mL×3). The organic layer was concentrated and the residue was purified by silica gel column chromatography eluting with DCM/CH3OH (20/1) to give product the title compound as a colorless oil (240 mg, yield: 69%). ESI-MS (M+H+): 351.2. 1H NMR (400 MHz, CDCl3) δ: 7.70 (dd, 2H), 7.68 (s, 1H), 7.41 (dd, 1H), 7.13 (d, 2H), 4.30-4.23 (m, 1H), 4.05 (s, 2H), 3.57 (s, 2H), 2.26 (d, 2H), 1.90 (d, 2H), 1.48-1.42 (m, 2H), 1.20-1.09 (m, 3H), 0.90 (s, 9H).

Workup

  1. extractionThe mixture was extracted with DCM (20 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography
  4. washeluting with DCM/CH3OH (20/1)

Sources & evidence

ORD record
ord-d34ca91bbd5a447ea57648605b4b8470
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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