Ammonium Chloride → HCID 5351709, compound

HRID 1050291Notes

Reaction equation

HRID 1050291 reaction equation
[N:1]([C@@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1.CCOCC>[NH2:1][C@@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 11004210HCID 11004210, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 5351709HCID 5351709, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.04 g (4.83 mmol) 3α-azido-5α-cholestane in 50 ml THF, 16 ml (16 mmol) of a 1M solution of LiAlH4 in ether are carefully added dropwise. The mixture is heated for 4 h under reflow, cooled to RT, followed by cautious addition of 5 ml of a saturated NH4Cl solution. After filtration and washing of the residual filtrate twice with ether, the ether phase is dried over Na2SO4 and concentrated. The amine is obtained as white solid and directly processed further. Yield 96%, F=95-97° C. C27H49N (387.7), calc. C, 83.65; H, 12.74; N, 3.61. found: C, 83.30; H, 12.42; N, 3.65.

Workup

  1. temperatureThe mixture is heated for 4 h under reflow
  2. filtrationAfter filtration
  3. washwashing of the residual filtrate twice with ether
  4. dry with materialthe ether phase is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4eb80ebd16da4a50945253bb0b77c451
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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