Water → HCID 66973987, compound

HRID 917150Notes

Reaction equation

HRID 917150 reaction equation
C([C:4]1[CH:37]=[CH:36][C:7]2[C:8](=[CH:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][C:23]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)([OH:26])[C:22]([CH3:35])([CH3:34])[CH2:21]3)[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3O[CH2:12][C:6]=2[N:5]=1)C=C.[CH2:38]1C[O:41][CH2:40][CH2:39]1.[OH2:43].S(=O)(O)[O-:45].[Na+]>O=[Os](=O)(=O)=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:23]2([OH:26])[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH:17]=[C:8]3[C:7]4[CH:36]=[CH:37][CH:4]=[N:5][C:6]=4[CH2:12][O:43][C:10]4[CH:13]=[CH:14][C:15]([CH2:38][CH:39]([OH:45])[CH2:40][OH:41])=[CH:16][C:9]3=4)[CH2:21][C:22]2([CH3:34])[CH3:35])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23665763Sodium BisulfiteHCID 66973942HCID 66973942, compound

Product 1

HCID 66973987HCID 66973987, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Conditions

Temperature
0 °C

Procedure

1-[3-(Allyl-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-4-(4-chloro-phenyl)-3,3-dimethyl-piperidin-4-ol (0.044 g, 0.08 mmol) was dissolved THF (2 mL)/H2O (0.5 mL) and cooled to 0° C. To the solution was added OsO4 (1.07 mL-2.5% OsO4 in t-butanol) and stirred at room temperature for 4 h. The reaction was diluted with sat. sodium bisulfite, the organics were removed dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (5% methanol/95% methylene chloride to 7.5% methanol/92.5% methylene chloride to 15% methanol/85% methylene chloride) to yield the title compound (0.025 g, 53%). 1H-NMR (CDCl3): δ 0.74 (ss 3H), 0.87 (s, 3H), 1.22 (d, 1H), 1.41 (s, 1H), 1.44 (d, 1H), 2.26–2.77 (m, 9H), 3.53 (d, 1H), 3.70 (dd, 1H), 3.93 (s, 1H), 5.30 (bs, 2H), 6.14 (t, 1H), 6.79 (d, 1H), 7.02 (d, 1H), 7.16 (s, 1H), 7.27 (d, 3H), 7.37 (d, 2H), 7.58 (d, 1H), 8.48 (dd, 1H). ESI-MS m/z: 515 (M+1), retention time 1.72.

Workup

  1. customthe organics were removed
  2. dry with materialdried over Mg2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. custompurified by Biotage flash chromatography (5% methanol/95% methylene chloride to 7.5% methanol/92.5% methylene chloride to 15% methanol/85% methylene chloride)

Sources & evidence

ORD record
ord-a456d8fe04b647ff911eaa7b5e4fbde4
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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