Ammonium Chloride → HCID 19390053, compound

HRID 1757231Notes

Reaction equation

HRID 1757231 reaction equation
[BH4-].[Na+].[C:3]([O:6][CH:7]1[CH2:19][CH2:18][C:10]2([CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH2:8]1)(=[O:5])[CH3:4].[Cl-].[NH4+]>CO>[OH:17][CH2:16][CH:13]1[CH2:12][CH2:11][C:10]2([CH2:9][CH2:8][CH:7]([O:6][C:3](=[O:5])[CH3:4])[CH2:19][CH2:18]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 19389999HCID 19389999, compound

Product 1

HCID 19390053HCID 19390053, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.110 g) was added, at 0° C. and under nitrogen atmosphere, to a solution of 1.35 g of 9-acetoxy-3-formyl-spiro[5.5]undecane (IV) in 50 ml of methanol. After 2 hrs, 10 ml. of a saturated aqueous ammonium chloride solution were added and the resulting mixture evaporated under reduced pressure. The residue, dissolved in 150 ml. of ethyl acetate, was washed with water to neutral pH; the organic layer, dried over anhydrous sodium sulfate, was evaporated under reduced pressure to give 1.50 g of 9-hydroxymethyl-3-acetoxy-spiro[5.5]undecane used as such in the following step. TLC: Rf=0.35 (SiO2 plates, diethylether/n-hexane 55/45). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 4.73 (1H, hept), 3.47 (2H, d), 2.03 (3H, s) 1.90-0.95 (17H, m).

Workup

  1. customthe resulting mixture evaporated under reduced pressure
  2. dissolutionThe residue, dissolved in 150 ml
  3. washof ethyl acetate, was washed with water to neutral pH
  4. dry with materialthe organic layer, dried over anhydrous sodium sulfate
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-74f80d68a5ff4c9c87bedfa37e9b2628
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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