Methanol → HCID 16730115, compound

HRID 1873663Notes

Reaction equation

HRID 1873663 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[NH:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:16]([NH:23][C:24](=[O:26])[CH3:25])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][N:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:16]([NH:23][C:24](=[O:26])[CH3:25])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 887MethanolHCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 58966608HCID 58966608, compound

Product 1

HCID 16730115HCID 16730115, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-dimethylbutyraldehyde (13 mg, 0.13 mmol) and the spiro-piperidine (B5) (25 mg, 0.10 mmol) in dry dichloromethane (2 ml) was stirred at room temperature for 30 min, cooled with ice-bath, and treated with sodium triacetoxyborohydride (44 mg, 0.2 mml), followed by acetic acid (1 drop) and methanol (1 ml). The reaction mixture was stirred for another 5 hours and concentrated under a stream of nitrogen. The residue was dissolved in methanol (1 ml) and purified by reverse phase HPLC to give the title compound no. 17 as a TFA salt. LC-MS: m/e=343.30 (M+H). Rt=1.63 min. 1H-NMR (500 MHz, DMSO-d6): 9.28 (br.s, 1H), 8.18 (d, 1H), 7.35 (d, 1H), 7.30 (t, 1H), 7.19 (t, 1H), 7.16 (d, 1H), 4.92 (m, 1H), 3.45 (m, 2H), 3.14 (m, 4H), 2.19 (m, 2H), 2.05 (m, 1H), 1.87 (s, 3H), 1.82 (m, 2H), 1.73 (d, 1H), 1.60 (m, 3H), 0.93 (m, 9H).

Workup

  1. temperaturecooled with ice-bath
  2. concentrationconcentrated under a stream of nitrogen
  3. dissolutionThe residue was dissolved in methanol (1 ml)
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-6ab2180d222345dc9c91d8b372419bfa
Source dataset
uspto-grants-2012_11
Patent number
US08304423B2

Reaction notes

Loading…