Methanol → HCID 71116049, compound

HRID 1423838Notes

Reaction equation

HRID 1423838 reaction equation
[CH3:1][C:2]1([CH:18]=[O:19])[CH2:17][CH2:16][CH2:15][C:4]2([O:8][C:7](=[O:9])[N:6]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5]2)[CH2:3]1.CO.[BH4-].[Na+]>C1COCC1>[OH:19][CH2:18][C:2]1([CH3:1])[CH2:17][CH2:16][CH2:15][C:4]2([O:8][C:7](=[O:9])[N:6]([CH2:10][C:11]([CH3:13])([CH3:14])[CH3:12])[CH2:5]2)[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86718791HCID 86718791, compound

Product 1

HCID 71116049HCID 71116049, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 7-methyl-3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decane-7-carbaldehyde intermediate product from step 1 (7.19 g, 26.9 mmol) was dissolved in THF (108 mL) and MeOH (27 mL) and treated with sodium borohydride (1.22 g, 32.3 mmol). The reaction was stirred at rt for 2 h and quenched with water (1 mL) and 1 N HCl (75 mL). The product was extracted into EtOAc (2×100 mL). The combined organics were dried over Na2SO4, filtered, and concentrated onto florisil for purification on a 120 g silica gel column (10-50% EtOAc/hexanes, 30 min gradient; 50% EtOAc/hexanes, 10 min; 50-75% EtOAc/hexanes, 10 min gradient; 85 mL/min elution; 254 nm detection) to afford the title compound (6.23 g, 75% combined yield with step 1). 1H NMR (400 MHz, CDCl3) δ 3.30-3.38 (m, 2H), 3.29 (s, 2H), 3.06 (d, J=14.05 Hz, 1H), 2.94 (d, J=14.05 Hz, 1H), 1.95-2.03 (m, 1H), 1.64-1.72 (m, 1H), 1.53-1.64 (m, 3H), 1.29-1.43 (m, 3H), 1.09 (s, 3H), 0.96 (s, 9H). MS (m/z) 270.2 (M+H+).

Workup

  1. customquenched with water (1 mL) and 1 N HCl (75 mL)
  2. extractionThe product was extracted into EtOAc (2×100 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated onto florisil for purification on a 120 g silica gel column (10-50% EtOAc/hexanes, 30 min gradient; 50% EtOAc/hexanes, 10 min; 50-75% EtOAc/hexanes, 10 min gradient; 85 mL/min elution; 254 nm detection)

Sources & evidence

ORD record
ord-ad6f32b588d24dd0ab3480f1b6ba048a
Source dataset
uspto-grants-2015_01
Patent number
US08927585B2

Reaction notes

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