Ammonia → HCID 13075708, compound

HRID 2198540Notes

Reaction equation

HRID 2198540 reaction equation
[Li].N.[F:3][C:4]([F:38])([F:37])[C:5]([OH:36])([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:35])[C@@H:25]4[O:34][C@@H:26]42)[CH:21]=[CH:20]3)[CH2:17][CH2:16]1)[CH3:14])[C:6]([F:9])([F:8])[F:7].[NH4+].[Cl-]>C1COCC1>[F:3][C:4]([F:37])([F:38])[C:5]([OH:36])([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@H:24]([CH2:25][C@@H:26]2[OH:34])[OH:35])=[CH:21][CH2:20]3)[CH2:17][CH2:16]1)[CH3:14])[C:6]([F:7])([F:9])[F:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 13075706HCID 13075706, compound

Product 1

HCID 13075708HCID 13075708, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.2 g of lithium in 80 ml of liquid ammonia (distilled over Na) was added 443 mg of the epoxide (4) in THF (70 ml) dropwise during 1 hr under dry ice-acetone bath cooling and then the reaction mixture was stirred for 1 hr at reflux. The reaction mixture was recooled by dry ice-acetone bath and to this was added solid NH4Cl (12 g) in small portions during 1 hr, then refluxed for 3 hr. After bubbling argon gas to remove NH3, water was added to the reaction mixture and this was extracted with AcOEt. The extract was submitted to silica gel column chromatography. The fraction eluted with n-hexane and AcOEt (1:2) afforded 274 mg (65%) of the triol (5), mp 201°-202° C. (from CHCl3), MS Calcd. for C27H40F6O3 : 526.2879. Found: 526.2878. NMR(CDCl3) and acetone-D6 δ0.69(s, 18-H3), 0.93(d, J=6 Hz, 21-H3), 1.03(s, 19-H3), 3.83(1H, m, 1-H), 4.00(1H, m, 3-H), 5.53(1H, m, 6-H).

Workup

  1. temperaturecooling
  2. temperatureat reflux
  3. customThe reaction mixture was recooled by dry ice-acetone bath
  4. temperaturerefluxed for 3 hr
  5. customAfter bubbling argon gas
  6. customto remove NH3, water
  7. additionwas added to the reaction mixture
  8. extractionthis was extracted with AcOEt
  9. washThe fraction eluted with n-hexane and AcOEt (1:2)

Sources & evidence

ORD record
ord-652cbe81afaf4981b270e76f2cb87761
Source dataset
uspto-grants-1982_11
Patent number
US04358406

Reaction notes

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