Sodium borohydride → HCID 18958698, compound

HRID 1708343Notes

Reaction equation

HRID 1708343 reaction equation
[OH:1][C:2]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.[BH4-].[Na+]>>[OH:7][CH2:6][CH2:5][N:4]([CH2:3][CH:2]([OH:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:8]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 18958702HCID 18958702, compound

Product 1

HCID 18958698HCID 18958698, compound

Conditions

Temperature
0 °C

Procedure

To 2-Hydroxy-4-methyl-2-pentadecylmorpholine (1 g, 3.06 mmol) at 0° C. was added NaBH4 (349 mg, 9.17 mmol) over a period of 10 minutes at 0° C., and the reaction mixture was stirred at 0° C. for 6 hours. Then methanol was removed by rotavap, the residue was taken in ether (100 mL) washed with water (2×25 mL), brine, and dried over sodium sulphate. Evaporation of the solvent gave a pure product. Yield (0.98 g, 97%), NMR 1H (CDCl3, 200 MHz) 0.89 (3H, t, CH3) 1.25 (26H, s, CH2) 1.38 (2H, m. CH2) 2.32 (3H, s, N--CH3) 2.3-2.7 (4H, m, CH2) 3.67 (3H, m, CH2OH, CHOH). NMR 13C (CDCl3, 50 MHz) 67.6 64.1, 59.7, 59.3 42.4, 34.9, 31.9, 29.7, 29.3, 25.6, 22.7, 14.1 IR cm--1 3392, 2922, 2853, 1466, 1265, 878, 740.

Workup

  1. customThen methanol was removed by rotavap
  2. washwashed with water (2×25 mL), brine
  3. dry with materialdried over sodium sulphate
  4. customEvaporation of the solvent
  5. customgave a pure product
  6. customYield (0.98 g, 97%), NMR 1H (CDCl3, 200 MHz) 0.89 (3H, t, CH3) 1.25 (26H, s, CH2) 1.38 (2H, m. CH2) 2.32 (3H, s, N--CH3) 2.3-2.7 (4H, m, CH2) 3.67 (3H, m, CH2OH, CHOH)

Sources & evidence

ORD record
ord-737f9f7b3cf04cff9096298b0c00b5b9
Source dataset
uspto-grants-1994_10
Patent number
US05358942

Reaction notes

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