(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine → (3R,5S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-3-ol

Participants

Role	Name	HCID	Charge
Reactant	(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine	HCID 18639173	—
Reactant	benzyl (2S,4R)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-hydroxypyrrolidine-1-carboxylate	HCID 57280098	—
Reactant	(11S,11aS)-11-Hydroxy-7-iodo-2-methylidene-10-(2,2,2-trichloroethyloxycarbonylamino)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one	HCID 69462904	—
Catalyst	Palladium	HCID 23938	—
Solvent	Ethanol	HCID 702	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(3R,5S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-3-ol	HCID 11481662	—

Reaction Steps

A slurry of 10% Pd/C (190 mg) in ethyl acetate (20 mL) was added to a solution of TBDMS ether (43) (1.90 g, 5.19 mmol) in ethanol (100 mL). The reaction mixture was hydrogenated (Parr apparatus) for 16 h. The catalyst was removed by vacuum filtration through Celite and excess solvent was evaporated under reduced pressure to give a yellow oil in quantitative yield (1.20 g, 100%). [α]22.2D=+35.6° (c 0.042,CHCl3). 1H NMR (CDCl3): δ −(0.07-0.08) (m, 6H, H1=, H2=), 0.82 (s, 9H, H3=, H4=, H5=), 1.68-1.73 (m, 2H, H1,), 2.99-3.11 (m, 2H, H11), 3.47-3.50 (m, 3H, H11a, H3), 4.09 (bs, 1H, NH or OH), 4.32 (bs, 1H, NH or OH). 13C NMR (CDCl3): δ −5.4 (C3=, C5=, C6=), 18.1 (C4=), 25.8 (C1=, C2=), 37.4 (C1), 54.6 (C11), 58.1 (C2), 64.6 (C3), 72.2 (C11a). IR (thin film): v=3330 (OH), 2928, 2857, 1557, 1421, 1331 (C—CH3), 1249 (CH3-Si), 1204 (t-Bu), 1191 (t-Bu), 1100 (Si—O), 1073, 993, 713 cm−1. MS (Cl) m/e (relative intensity): 232 (M+., 100), 230 (13), 174 (5), 133 (6), 86 (6).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07265105B2
Source dataset	uspto-grants-2007_09
ORD ID	ord-0ea49f68c518412cae3c8e35ef233846
Source note	uspto-grants-2007_09