Water → HCID 13957896, compound

HRID 1761349Notes

Reaction equation

HRID 1761349 reaction equation
[F:1][CH:2]([F:23])[C:3]1[C:8]([C:9]([O-])=[O:10])=[C:7]([CH2:12][CH3:13])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]([C:19]([F:22])([F:21])[F:20])[N:4]=1.B.O>O1CCCC1>[F:23][CH:2]([F:1])[C:3]1[N:4]=[C:5]([C:19]([F:22])([F:20])[F:21])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([CH2:12][CH3:13])[C:8]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 86742963HCID 86742963, compound

Product 1

HCID 13957896HCID 13957896, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a dry 500 ml four-necked flask is charged 30.6 g (0.09 mole) of the product of Example 28 and 40 ml of tetrahydrofuran under nitrogen. The reaction mixture is cooled to 10° C. with an ice-water bath. To the above solution is added via a syringe 180 ml (0.18 mole) of 1M borane in tetrahydrofuran. The reaction mixture is stirred for 160 hours and poured into water. The organics are extracted into 300 ml of ether and the ether extract washed with 200 ml of saturated sodium bicarbonate, dried (MgSO4), and concentrated. The residue is crystallized from petroleum ether to give 25 g (84.9%) of the desired product, m.p. 59.5°-60.5° C.

Workup

  1. extractionThe organics are extracted into 300 ml of ether
  2. extractionthe ether extract
  3. washwashed with 200 ml of saturated sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-da0fae40aa224ca38a58cc7f6a9f862a
Source dataset
uspto-grants-1989_05
Patent number
US04826530

Reaction notes

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