Dichloromethane → [4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-methanol

HRID 1794796Notes

Reaction equation

HRID 1794796 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.C(Cl)Cl>CO.O1CCCC1>[O:6]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]3[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 27643354-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 10586716[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (3.78 g, 100 mmol) was added in four portions to a stirred solution of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde (4.94 g, 20 mmol) (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) in methanol/tetrahydrofuran (1:1, 100 mL) at 0° C. and the resulting solution was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. Methylene chloride was added and the solution was washed with water and dried over sodium sulfate. The solvents were removed and the residue was solidified upon standing (5.0 g, 100%); 1H NMR (300 MHz, CDCl3) δ 1.84 (t, J=5.7 Hz, 4 H), 3.33 (t, J=5.7 Hz, 3.99(s, 4 H), 4.59 (d, J=5.8 Hz, 2 H), 6.93 (d, J=8.7 Hz, 2 H), 7.24 (d, J=8.7 Hz, 2 H); MS (ES) m/z: 249.9 (MH+); HRMS Calcd. for C14H20NO3(MH+): 250.1443. Found: 250.1434.

Workup

  1. waitat room temperature for 1 hour
  2. washthe solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed

Sources & evidence

ORD record
ord-ae91d0aecbb34be3a3c21e4f33625d7e
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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