Methanol → HCID 58562554, compound

HRID 1896826Notes

Reaction equation

HRID 1896826 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[CH2:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+].C[OH:25]>>[OH:25][CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]1[CH2:7][CH2:6][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58562846HCID 58562846, compound

Product 1

HCID 58562554HCID 58562554, compound

Conditions

Temperature
-78 °C

Procedure

A 250 mL round bottom flask was charge with tert-butyl (1-(1,4-dioxaspiro[4.5]decan-8-yl)allyl)carbamate (5.8 g, 18.6 mmol) and methanol (207 mL). The mixture was cooled to −78° C. and ozone was bubble through the solution at a rate of 3 L/min for 1 hour. The mixture turned pale blue in color after 30 minutes. After 1 hour air was bubble through the solution for 30 minutes until the blue color disappeared. Sodium borohydride (2.82 g, 74.5 mmol) was added to the mixture in 4 portions. The mixture was gradually warmed to room temperature. After 6 h at room temperature the mixture quenched with saturated aqueous ammonium chloride. Dilute with water and extract with ethyl acetate. Dry organic layer with MgSO4, filter, and concentrate in vacuo to give tert-butyl (3-hydroxy-1-(1,4-dioxaspiro[4.5]decan-8-yl)propyl)carbamate (5.1 g, 16.2 mmol) as a clear oil.

Workup

  1. customozone was bubble through the solution at a rate of 3 L/min for 1 hour
  2. customAfter 1 hour air was bubble through the solution for 30 minutes until the blue color
  3. temperatureThe mixture was gradually warmed to room temperature
  4. customAfter 6 h at room temperature the mixture quenched with saturated aqueous ammonium chloride
  5. additionDilute with water
  6. extractionextract with ethyl acetate
  7. filtrationDry organic layer with MgSO4, filter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-433e24ef0f1b44d0a95429416c6cd1b1
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…