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1,2-Dichloroethane → HCID 18461095, compound

HRID 2303331
Notes
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Reaction equation

HRID 2303331 reaction equation
[CH2:1]([CH:8]1[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]=O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([CH:8]1[CH2:14][CH:13]2[N:15]([CH2:32][CH2:31][CH2:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:25][CH:26]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 563558HCID 563558, compoundHCID 5049666Sodium triacetoxyborohydrideHCID 18461105338733-58-7

Product 1

HCID 18461095HCID 18461095, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.18 g of 3-benzyl-8-aza-bicyclo[3.2.1]octane, 0.30 g of 3-(4-benzyloxy-phenyl)-propionaldehyde, 5 mL of 1,2-dichloroethane and 0.3 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was diluted with 50 mL chloroform and 10 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography eluting with 80:20 EtOAc:MeOH gave 0.28 g of 3-benzyl-8-[3-(4-benzyloxy-phenyl)-propyl]-8-aza-bicyclo[3.2.1]octane as a 2:1 mixture of exo:endo isomers. Hydrogenation at 1 atm over 0.2 g of 10% Pd/C in 50 mL of ethanol gave 0.17 g of 4-[3-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-phenol as a 2:1 mixture of exo:endo isomers: MS (m+1)=336.4; 1H NMR (400 MHz, CDCl3) 7.25-7.1 (complex, 5H), 6.8 (d, 2H), 6.5 (d, 2H), 3.35 (br s, 2H), 2.75 (d, 0.6 H), 2.5-2.3 (complex, 5.4 H), 2.1 (m, 2H), 1.95 (m, 1H), 1.85 (m, 3H), 1.5 (m, 3H), 1.4 (m, 2H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with 80:20 EtOAc

Sources & evidence

ORD record
ord-108dcb182bec4d6ab5d7041b4b69d7ca
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06432976B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes