Methanol → HCID 58562767, compound

HRID 1896823Notes

Reaction equation

HRID 1896823 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]=C)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+].C[OH:25]>>[OH:25][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58562846HCID 58562846, compound

Product 1

HCID 58562767HCID 58562767, compound

Conditions

Temperature
-78 °C

Procedure

A 250 mL round bottom flask was charged with tert-butyl (1-(1,4-dioxaspiro[4.5]decan-8-yl)allyl)carbamate (5.3 g, 17.8 mmol), prepared in the previous step, and methanol (198 mL). The mixture was cooled to −78° C. and ozone was bubbled 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 bubbled through the solution for 30 minutes until the blue color disappeared. Sodium borohydride (2.7 g, 71.3 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. After dilution with water and extraction with ethyl acetate, the organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the product as a clear oil.

Workup

  1. customozone was bubbled through the solution at a rate of 3 L/min for 1 hour
  2. customAfter 1 hour air was bubbled 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. extractionAfter dilution with water and extraction with ethyl acetate
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df3bb1096d2d4acda65172f15c8ddd08
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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