Ammonium Chloride → HCID 19696324, compound

HRID 641705Notes

Reaction equation

HRID 641705 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][N:5]12.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][N:5]12

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15063399HCID 15063399, compound

Product 1

HCID 19696324HCID 19696324, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of the product of Step 5 (12 g) in 150 mL of MeOH was added 2 g of NaBH4. After stirring for 30 min at 0° C., 100 mL of saturated aqueous solution of NH4Cl was added and the mixture was extracted with EtOAc (500 mL). The extract was dried over Na2SO4 and filtered. The filtrate was concentrated to give the crude title compound which was used for next step without further purification. 1H NMR (500 MHz, acetone-d6) δ 7.46 (d, 1H), 7.30 (d, 1H), 7.07 (t, 1H), 7.00 (t, 1H), 6.15 (s, 1H), 4.40 (m, 1H), 4.25 (dd, 1H), 3.91 (dd, 1H), 3.20 (m, 1H), 2.46 (m, 1H), 2.10 (m, 1H). 2.00 (m, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc (500 mL)
  2. dry with materialThe extract was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b7abf640e4944aa5a413267746480b05
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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