Ammonium formate → HCID 66885811, compound

HRID 2204053Notes

Reaction equation

HRID 2204053 reaction equation
[CH2:1]([O:4][C@H:5]([C@@H:25]([O:38][CH2:39][CH:40]=[CH2:41])[C@H:26]([O:34][CH2:35][CH:36]=[CH2:37])[C:27](=O)[CH2:28][O:29][CH2:30][CH:31]=[CH2:32])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[CH:9]=1)=O)[CH:2]=[CH2:3].C([O-])=O.[NH4+].[BH3-]C#[N:48].[Na+]>CO>[CH2:35]([O:34][C@H:26]1[C@H:25]([O:38][CH2:39][CH:40]=[CH2:41])[C@@H:5]([O:4][CH2:1][CH:2]=[CH2:3])[C@H:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=3)[CH:9]=2)[NH:48][C@@H:27]1[CH2:28][O:29][CH2:30][CH:31]=[CH2:32])[CH:36]=[CH2:37]

Participants

5

Reactant 3

HCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydrideHCID 66885708HCID 66885708, compound

Product 1

HCID 66885811HCID 66885811, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound from Step E (0.60 g, 1.03 mmol) in MeOH (12 ml) was added 4 Å MS followed by ammonium formate (0.13 g, 2.06 mmol). NaBH3CN (0.14 g, 2.3 mmol) was then added in one portion and the mixture stirred at room temperature for 1 hour 30 minutes. The reaction mixture was then filtered and concentrated. Purification by silica gel chromatography (10%-20% EtOAc/hexanes) afforded (2R,3R,4R,5S,6S)-3,4,5-tris-allyloxy-2-allyloxymethyl-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-piperidine (155 mg, 0.27 mmol, 27%). MS (ES+) [M+H]+=568.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (10%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dbc025dfc0d34d3388af588a9a37bd00
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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