Ammonium Chloride → HCID 86714086, compound

HRID 576410Notes

Reaction equation

HRID 576410 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[C:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=3)[C:34]([Cl:47])=[C:33]([O:48]CC=C)[C:32]=2[O:52]CC=C)[O:11][C@@H:10]1[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:47][C:34]1[C:35]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=2)=[CH:36][C:31]([C@H:12]2[C@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([CH2:56][O:57][CH2:58][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)[O:11]2)=[C:32]([OH:52])[C:33]=1[OH:48]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86714087HCID 86714087, compound

Product 1

HCID 86714086HCID 86714086, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 203 (2.82 g, 2.06 mmol) in THF (20 mL) were added NaBH4 (0.23 g, 6.00 mmol) and Pd(PPh3)4 (0.23 g, 0.20 mmol) at 0° C. The mixture was warmed up to r.t. slowly and stirred at r.t. for 12 h. The mixture was cooled to 0° C. and aq. sat'd NH4Cl solution (50 mL) was added to the mixture slowly. The mixture was extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 204 (1.42 g, 86%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-096a6c888a2d43f0aabd9e4ac0c5e639
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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