Dichloromethane → Chloride

HRID 1827578Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]=O)=[CH:21][CH:20]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+].C(Cl)[Cl:57]>>[Cl-:57].[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:21][CH:20]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8]

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 31268Pyrrolidine

HCID 516892Sodium Bicarbonate

HCID 5049666Sodium triacetoxyborohydride

HCID 22137280HCID 22137280, compound

Product 2

HCID 312ChlorideYield 15%

HCID 10051354HCID 10051354, compound

Procedure

To a solution of N-(3-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.050 g, 0.11 mmol) in 2 mL methylene chloride was added pyrrolidine (0.010 g, 0.14 mmol) and NaB(OAc)3H (0.045 g, 0.21 mmol). The reaction mixture was stirred at room temperature for three days. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (15% methanolmethylene chloride) afforded 0.034 g of the title compound. MS 493.3 (M+1)+

Workup

washthe aqueous solution was washed with methylene chloride
dry with materialThe organic layer was dried (magnesium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-7ae6d9b43ea3409496b1fe83e6eab244
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053212B2

Reaction notes

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