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Sodium triacetoxyborohydride → 2-(2,6-dichlorophenyl)-N-((1-methylcyclobutyl)methyl)-2-((triethylsilyl)oxy)ethanamine

HRID 2202684
Notes
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Reaction equation

HRID 2202684 reaction equation
[CH3:1][C:2]1([CH:6]=O)[CH2:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH:16]([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:17][NH2:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH:16]([O:19][Si:20]([CH2:21][CH3:22])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:17][NH:18][CH2:6][C:2]1([CH3:1])[CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 201345271-Methylcyclobutane-1-carbaldehydeHCID 1238562512-(2,6-Dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine

Product 1

HCID 1239798292-(2,6-dichlorophenyl)-N-((1-methylcyclobutyl)methyl)-2-((triethylsilyl)oxy)ethanamineYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture of 1-methylcyclobutanecarbaldehyde (38.3 mg, 0.390 mmol) in DCM (2.0 ml) was added 2-(2,6-dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine (125 mg, 0.390 mmol) followed by NaBH(OAc)3 (124 mg, 0.585 mmol). After 45 min, this was quenched with sat. aq. NaHCO3. The layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were concentrated and then purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichlorophenyl)-N-((1-methylcyclobutyl)methyl)-2-((triethylsilyl)oxy)ethanamine (89 mg, 0.221 mmol, 56.7% yield). 1H NMR (500 MHz, CDCl3) δ 7.18-7.22 (m, 2H), 6.98-7.10 (m, 1H), 5.57 (br. s., 1H), 3.30 (t, J=10.70 Hz, 1H), 2.74 (br. s., 1H), 2.60 (br. s., 1H), 2.51 (d, J=10.03 Hz, 1H), 1.68-1.89 (m, 4H), 1.60 (br. s., 2H), 1.47 (br. s., 1H), 1.03-1.14 (m, 3H), 0.76-0.84 (m, 9H), 0.41-0.54 (m, 6H); LCMS (ESI) m/z 402.4 (M+H)+.

Workup

  1. customthis was quenched with sat. aq. NaHCO3
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. concentrationThe combined organic layers were concentrated
  5. custompurified by prep TLC
  6. washeluted with 5% MeOH/DCM

Sources & evidence

ORD record
ord-827326e76c1c4b498551ab6fb954ed28
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365522B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes