Ammonium Chloride → HCID 11047710, compound

HRID 1744222Notes

Reaction equation

HRID 1744222 reaction equation
[CH2:1]([C@@H:4]1[C@H:9]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:7]2([CH3:8])[C:6](=[O:30])[CH2:5]1)[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH:2]=[CH2:3].[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.O>[CH2:1]([C@@H:4]1[C@H:9]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:7]2([CH3:8])[C@@H:6]([OH:30])[CH2:5]1)[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10960374HCID 10960374, compound

Product 1

HCID 11047710HCID 11047710, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 341 mg (0.850 mmol) of 71, 129 mg (3.40 mmol) of NaBH4 in THF (9 mL) with 37 drops of H2O was stirred at rt for 3 h, poured into saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (3×, 50 mL). Combined organic extracts were washed with 10% Na2S2O5 (30 mL), H2O (30 mL), dried over Na2SO4 and concentrated in vacuo giving a yellow oil. Purification by flash chromatography on a 3×21 cm column of silica gel using 2:1 hexanes/EtOAc as eluent gave 311 mg (91%) of 72. Data for 72: TLC, T-1, Rf 0.37; 1H NMR (500 MHz, CDCl3) δ 0.83 (s, 3H, H-18), 1.02 (t, 1H, J=10.3 Hz, H-14), 3.70 (t, 1H, J=9.2 Hz, H-17α), 5.01–5.06 (m, 2H, ═CH2), 5.04 (s, 2H, benzylic-H), 5.78–5.86 (m, 1H, —CH═), 6.72 (d, 1H, J=2.7 Hz, H-4), 6.79 (dd, 1H, J=8.6, 2.7 Hz, H-2), 7.22 (d, 1H, J=8.6 Hz, H-1), 7.31–7.44 (m, 5H, Ar—H).

Workup

  1. extractionextracted with EtOAc (3×, 50 mL)
  2. washCombined organic extracts were washed with 10% Na2S2O5 (30 mL), H2O (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customgiving a yellow oil
  6. customPurification by flash chromatography on a 3×21 cm column of silica gel using 2:1 hexanes/EtOAc as eluent

Sources & evidence

ORD record
ord-8ad1a1ea037f480da8d5bb5019bab41b
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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